methyl 5-methoxy-2-methyl-1H-indole-3-acetate synthesis
- Product Name:methyl 5-methoxy-2-methyl-1H-indole-3-acetate
- CAS Number:7588-36-5
- Molecular formula:C13H15NO3
- Molecular Weight:233.26
67-56-1
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7588-36-5
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Yield:7588-36-5 100%
Reaction Conditions:
Stage #1: 5-Methoxy-2-methylindole-3-acetic acidwith bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride;triethylamine in dichloromethane at 20; for 0.0833333 h;
Stage #2: methanol in dichloromethane at 20;
Steps:
General Procedure A_variant1:
General procedure: A reaction mixture containing the indoleacetic acid derivative (1 equivalent) and BOP-Cl (1 equivalent) in 3 mL/mmol of anhydrous CH2Cl2 is treated with triethylamine (2 equivalents) and aged at ambient temperature for 5 min. The mixture is combined with anhydrous methanol (0.14 mL/mmol) and then continuously stirred overnight at room temperature. Following dilution with dichloromethane (12 mL/mmol), the organic solution is washed with water (2x6 mL/mmol), dried over Na2SO4, and filtered. The organic filtrate is collected and concentrated in vacuo and the crude ester is purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to afford the title compound at first as viscous yellow oil, which stably crystallizes upon seeding and subsequent cold storage.
References:
Liedtke, Andy J.;Marnett, Lawrence J.;Kim, Kwangho;Stec, Donald F.;Sulikowski, Gary A. [Tetrahedron,2012,vol. 68,# 48,p. 10049 - 10058,10] Location in patent:supporting information Liedtke, Andy J.;Kim, Kwangho;Stec, Donald F.;Sulikowski, Gary A.;Marnett, Lawrence J. [Tetrahedron,2012,vol. 68,# 48,p. 10049 - 10058] Location in patent:supporting information
2882-15-7
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7588-36-5
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624-45-3
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19501-58-7
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7588-36-5
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$21.00/100mg
2882-15-7
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75-36-5
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7588-36-5
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![Pentanoic acid, 4-[2-(4-methoxyphenyl)hydrazinylidene]-, methyl ester](/CAS/20210305/GIF/53258-38-1.gif)
53258-38-1
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7588-36-5
74 suppliers
$21.00/100mg